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Flips Out, Funds In: Mike Simmons’ Pivot to Lending Millions | Ep 51
What does it take to build a thriving 7-figure real estate business and successfully pivot into hard money lending?
In this episode of Diehard Entrepreneur Stories, Devin Ramos talks with Mike Simmons, who grew a successful house flipping and wholesaling business over a decade before co-founding Express Hard Money. Mike shares his journey from corporate jobs to real estate entrepreneurship, the challenges of building scalable systems, and winning a 7-figure flipping contest in 10 months.
We discuss the shift from hands-on flipping to wholesaling for faster growth, managing sales teams, and navigating the ups and downs of marketing strategies—including overcoming the COVID-19 direct mail collapse.
Mike also dives deep into starting his lending company, how real estate experience shapes his approach, and the nuances of raising capital from family offices versus high net worth individuals. He reveals the importance of smooth customer experience over low interest rates, and lessons learned about fund administration and institutional investor expectations.
Entrepreneurs, real estate investors, and leaders will gain insights on resilience, scaling businesses, and pivoting to new growth opportunities.
Connect with Mike Simmons:
Website: mikesimmons.com
Express Hard Money: expresshardmoney.com
TIMESTAMPS
00:00 Introduction
06:00 From UPS and corporate to real estate entrepreneurship
14:00 Early flipping struggles and pivot to wholesaling
25:20 Losing contractor and realtor, discovering wholesaling potential
30:00 Marketing scale-up and hiring sales team
32:50 Joining Seven Figure Flipping and rapid growth to $1M
36:00 Challenges managing sales team and business systems
38:30 COVID-19 impact on direct mail marketing and recovery with PPC
42:00 Maintaining $1M revenue as a lifestyle business, scaling again in 2023-24
44:00 Managing partner dynamics and eventual amicable buyout
56:30 Launching Express Hard Money lending company
58:30 Lending niche insights: real estate experience benefits
1:01:00 Raising capital from family offices vs. high net worth individuals
1:14:30 Building proper fund administration and data room setup
1:18:00 Importance of professionalism and patience with institutional investors
1:22:00 Closing thoughts and where to find Mike Simmons online
🎬Watch this on Youtube:
https://youtu.be/I-2RIR5WRQ4
⚡ Let's stay in touch:
Instagram: https://www.instagram.com/devinramos/
Facebook: https://www.facebook.com/devinjramos035/
LinkedIn: https://www.linkedin.com/in/devin-ramos-602a811ab
🎬 Produced by: https://daretopodcast.com/
#RealEstate #HardMoneyLending #Entrepreneurship #RealEstateInvesting #HouseFlipping #Wholesaling #BusinessGrowth #InvestorTips #PassiveIncome #StartupLife #SmallBusiness #Leadership #DevInRamos #ForwardFactor #DiehardEntrepreneur
Hosted on Acast. See acast.com/privacy for more information.
View all episodes
By Devin RamosWhat does it take to build a thriving 7-figure real estate business and successfully pivot into hard money lending?
In this episode of Diehard Entrepreneur Stories, Devin Ramos talks with Mike Simmons, who grew a successful house flipping and wholesaling business over a decade before co-founding Express Hard Money. Mike shares his journey from corporate jobs to real estate entrepreneurship, the challenges of building scalable systems, and winning a 7-figure flipping contest in 10 months.
We discuss the shift from hands-on flipping to wholesaling for faster growth, managing sales teams, and navigating the ups and downs of marketing strategies—including overcoming the COVID-19 direct mail collapse.
Mike also dives deep into starting his lending company, how real estate experience shapes his approach, and the nuances of raising capital from family offices versus high net worth individuals. He reveals the importance of smooth customer experience over low interest rates, and lessons learned about fund administration and institutional investor expectations.
Entrepreneurs, real estate investors, and leaders will gain insights on resilience, scaling businesses, and pivoting to new growth opportunities.
Connect with Mike Simmons:
Website: mikesimmons.com
Express Hard Money: expresshardmoney.com
TIMESTAMPS
00:00 Introduction
06:00 From UPS and corporate to real estate entrepreneurship
14:00 Early flipping struggles and pivot to wholesaling
25:20 Losing contractor and realtor, discovering wholesaling potential
30:00 Marketing scale-up and hiring sales team
32:50 Joining Seven Figure Flipping and rapid growth to $1M
36:00 Challenges managing sales team and business systems
38:30 COVID-19 impact on direct mail marketing and recovery with PPC
42:00 Maintaining $1M revenue as a lifestyle business, scaling again in 2023-24
44:00 Managing partner dynamics and eventual amicable buyout
56:30 Launching Express Hard Money lending company
58:30 Lending niche insights: real estate experience benefits
1:01:00 Raising capital from family offices vs. high net worth individuals
1:14:30 Building proper fund administration and data room setup
1:18:00 Importance of professionalism and patience with institutional investors
1:22:00 Closing thoughts and where to find Mike Simmons online
🎬Watch this on Youtube:
https://youtu.be/I-2RIR5WRQ4
⚡ Let's stay in touch:
Instagram: https://www.instagram.com/devinramos/
Facebook: https://www.facebook.com/devinjramos035/
LinkedIn: https://www.linkedin.com/in/devin-ramos-602a811ab
🎬 Produced by: https://daretopodcast.com/
#RealEstate #HardMoneyLending #Entrepreneurship #RealEstateInvesting #HouseFlipping #Wholesaling #BusinessGrowth #InvestorTips #PassiveIncome #StartupLife #SmallBusiness #Leadership #DevInRamos #ForwardFactor #DiehardEntrepreneur
Hosted on Acast. See acast.com/privacy for more information.